On various transition metal catalysts (Raney nickel, Pd/C, Pd black, RuO2, Rh/C), the N-C(2) bond in N-benzoyl-2,2,4,4-tetraMe-azetidin-3-one (1) undergoes hydrogenolysis with 100% selectivity, as does that in the corresponding azetidine derivative 2 on Raney nickel; in the process, the oxo group in the ring in 1 is converted to a hydroxy group. In the analogues with higher numbers of ring atoms, only the latter hydrogenation proceeds; under identical reaction conditions, C-N hydrogenolysis does not occur. The rate of hydrogenolysis is increased by the carbonyl group at position 3 in azetidinone, as compared to that of azetidine, which does not possess the carbonyl function. A proposal is made concerning the reaction mechanism.
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